Skip to main content

A bareboat tour of Chesapeake Bay

It was the difference between making time and taking time. The last time we were on the Chesapeake was spring of 2002, when we made the trip from Beaufort, N.C., to Guilford, Conn. We were moving from Point A to point B in the shortest possible time. This past June, we decided to charter for a week on the Chesapeake. Our goal was to explore some of the Bay’s nooks and crannies in a leisurely fashion, and to check out some of the spots we hadn’t visited on our former trips.

The difference was between sailing our own boat and chartering. Three years earlier, we sailed aboard our shallow-draft, 35-foot Pearson, vintage 1971, a reliable and noble vessel that has carried us through some harrowing situations.

For our chartering experience, we sailed a 32-foot Beneteau out of Rock Hall, Md., which we chartered through Haven Charters. It was the difference between off-season on the Chesapeake and high season.

At any time, the Bay is a magnificent boating destination. But if you’re looking for splendid isolation, the high season is obviously not the best time to find it. Still, it can be found nonetheless.

Rock Hall began its life as a tobacco port of call in Colonial times, and later evolved into a fishing and crabbing center. Now, like other bayside communities, it is becoming more of a center for pleasure boating. One resident told us the town had 1,800 boat slips and 1,800 residents.

Rock Hall offers boaters both protection and proximity. Part of Rock Hall’s Harbor is appropriately named The Haven, but it’s only minutes from the Bay. For us, Rock Hall had the advantage, too, of being seven hours away from Connecticut — by car — as opposed to seven days by boat.

Haven Charters operates out of Haven Harbor Marina, tucked snugly into the easternmost part of the harbor. Jacqui and David Fife oversee a fleet of 22 boats, ranging from 32 to 42 feet. Haven Charters is well-run, orderly and friendly. As a sign proclaims when you enter Rock Hall, “Nice people live here,” and Jacqui and David fit the description.

We had decided on the 32-foot Beneteau because we have chartered Beneteaus before, and found them to be predictable and adequate vessels. We also wanted a boat that was small enough for two people to handle comfortably.

Chartering someone else’s boat means living with that owner’s equipment and setup. On our own boat we had tools and replacement supplies for every system — plumbing, electrical, mechanical — and, given the Pearson’s age, had occasion to use much of it. Our chartered Beneteau had two screwdrivers — Philips and straight-edge — a pair of pliers, and a Leatherman. Period. This was certainly a blow to our confidence in self-reliance and the ability to meet challenges out on the lonely waters.

Chartering also means taking the time to learn an unfamiliar boat, and even though a 32-foot Beneteau is relatively simple and straightforward, we used the sleepover the night before to begin to check out the systems (and to catch a great seafood dinner at the nearby Waterman’s Restaurant).

As it turned out, the next day brought a steady, hard rain, and we chose to stay at the slip through that day and night before setting out, a non-existent luxury when we had to make time on our last trip.

We departed on a Saturday morning. The day was warming, the winds were too light to sail, and the traffic on the Bay was moderate as we headed off to Kent Narrows. The approach to the Narrows from the north is dicey. The approach channel is quite narrow, and boats entering from either direction play a game of chicken to see who will capture the central and safer part of the channel. And then there are always some impatient powerboaters who have little tolerance for following a slowpoke sailboat. But we managed to arrive at the drawbridge with perfect timing. We never had to slow down or wait. Some things work out perfectly.

Once through the Narrows, we thought we would check out Crab Alley on Tilghman Island, but the skies darkened in the early afternoon and we decided instead to head straight for the Wye River on Maryland’s Eastern Shore. Seeking splendid isolation, we traveled up the Wye East, a branch of the Wye that is bordered on one side by the mostly state-owned Wye Island. The island is largely untouched; it has no public facilities, no marinas, no supplies, no landings — just blue herons, snowy white egrets, mallards, whistling swans, and a rare variety of squirrel, to name a few inhabitants. Although Dividing Creek off the Wye East is a favorite of boaters, the more isolated Granery Creek, a mile beyond, seemed promising.

Our cruising guide told us that Granery Creek might hold six to eight carefully anchored boats. When we arrived at 2:30 p.m. there were already five boats there, so we negotiated our spot and settled into what we thought would be a quiet and peaceful afternoon and evening. Before too long the tiny creek began to resemble a runway at Chicago’s O’Hare Airport, with boats entering every two minutes and no equivalent of an air traffic controller to guide them. “Rafting up” seemed to be the order of the day, and before long there were more than two dozen boats in rafting configurations of two, three, even seven together. It seemed that we had happened upon a gathering of an SOS — Singles on Sailboats. For the rest of the afternoon the dinghy travel was heavy and the partying was serious. Only one other boat was not rafted up. And we were even approached by a strange boat asking, “Are you looking for company?”

The parties on the boats moved to a party onshore at a rustic campground site. Rock-and-roll blared. Thankfully, however, the revelers were early to bed, and the anchorage was quiet well before 11 p.m.

The next morning dawned warm and hazy, with a mist rising off the creek. After a leisurely morning we decided to head off across the Bay and sample a spot on the Western Shore. A sunny and warm Sunday on the Bay draws boaters of every ilk, and by the time we approached the mouth of South River, just below Annapolis, we found that practicing “rules of the road” required some serious concentration. There were fishermen anchored and drifting, powerboats large and small, sailboats sailing and motoring and dead in the water, not to mention all the crab pot buoys.

Harness Creek is an anchorage about 2-1/2 miles from the mouth of the South River. It is bordered on one side by residences, but on the other by Quiet Waters Park, a 340-acre county park with high, wooded banks.

Again, seeking splendid isolation, we negotiated our entry to the creek. The shoals at the entry were much less of a hazard than were the 85 or so boats that had wedged themselves into the tiny creek. In addition to those who had arrived by boat, there were people who had arrived by car and who rented canoes, kayaks and paddleboats from the park concessionaire. A warm, sunny Sunday in June on the Chesapeake, and the water clearly beckoned everyone.

Between the time we anchored at 3 p.m. and sunset, however, the place had emptied out, and by dusk we were the only boat in view. Birds began to emerge from their daytime refuge. Ospreys stationed themselves on perches watching for dinner. And people in the homes flanking the western bank of the creek began to venture out. With the exception of us, the interlopers had gone home, and the inhabitants — animal and human — could reclaim their spot.

Nevertheless, the sound of go-fastboats on the South River continued long into the evening and well after dark. The South River’s reputation as the “drag strip of the Chesapeake’s Western Shore” still holds.

The next morning continued hot and increasingly humid. NOAA’s constant prediction of “chances of showers” changed to an ominous threat of high winds and violent thunderstorms in the late afternoon, so we decided to leave early and do our traveling well before any storm might hit. We were returning to the Eastern Shore, to the Chester River, just south of Rock Hall.

By 9:30 a.m. we were already at the Annapolis Bay Bridge, where we joined the container ships, barges, gravel boats and busy tenders. As we approached the bridge, we watched Naval Academy boats practicing their maneuvers.

The Chester, which is the second-longest river on the Eastern Shore, has four branches that are flanked by rolling countryside, large farms and lavish estates. We decided to head for Langford Creek, a branch across from the popular Corsica River.

Low on ice and wilting from the intense heat and humidity, we stopped at the Lankford Bay Marina before heading to the nearby Cacaway Island, a tiny, private, uninhabited island at the fork of the east and west branches of Langford Creek. Again, we were seeking splendid isolation, and this time we found it. We tucked in close to the island, jumped into the water to cool off, and monitored the weather forecast.

NOAA’s warnings became increasingly strident, and added to the warnings were the beeping and honking sounds of the emergency warning system. We listened to predictions of winds as high as 70 miles an hour, and hail the size of golf balls. The forecasts were worrisome, but largely theoretical until NOAA announced that the storm would hit Rock Hall at 7:25 p.m. By land we were 4-1/2 miles east of Rock Hall. NOAA had our attention. We had already done all of our battening down and stowing. All that remained was to watch the horizon to the northwest.

Right on time, the front hit at 7:35 p.m. The water’s surface became pea-green with mustard stipples, and the wind hit like a flat hand against the face. But our tiny island blocked the worst of the wind and our anchor held. We recorded winds of 35 miles an hour. And then the rain hit. Thankfully, there was no hail.

As the front moved over us, the sky became blacker than night. Sheets of rain swept over us, and the Bimini whipped up and down like plastic wrap. Then, as the storm lessened, the nighttime sky returned to its usual gray. Dinner was late that night.

The next morning the world looked washed clean, and our dinghy had 8 inches of water in it. The hot and humid weather persisted, and NOAA returned to its predictable “chance of showers” forecast. We decided that the very best place to be was right where we were, so we spent the day at anchor behind Cacaway Island — splendid isolation that included the luxury of going nowhere. We dinghied around the island and watched the numerous pairs of ospreys conducting their daily affairs.

For the last night of our charter we decided to travel back to Swan Creek, a lovely anchorage just up the water from Rock Hall. The business of Rock Hall is in contrast to the quiet of the Swan Creek anchorage, and we spent our last afternoon lazily. The heat continued unabated, and we heard on the radio that local schools were being let out early. On the water is the place to be in such conditions.

The next morning it was a quick trip back to our slip, where we readied the boat for turning it back in to Haven Charters. With the exception of the storm, the week had been blissfully relaxing and uneventful. As we turned the boat in and walked away, we were very much aware of the benefits of chartering rather than owning.

Our return to the Chesapeake confirmed our appreciation of this magnificent tidal estuary as the country’s premier boating destination. We took away some fine memories of several secluded and not-so-secluded anchorages in the northern Bay. And with 11,600 miles of coastline, the Chesapeake continues to beckon. We’ll be back.